CN107779207B - Liquid crystal alignment agent and application thereof - Google Patents
Liquid crystal alignment agent and application thereof Download PDFInfo
- Publication number
- CN107779207B CN107779207B CN201710691305.5A CN201710691305A CN107779207B CN 107779207 B CN107779207 B CN 107779207B CN 201710691305 A CN201710691305 A CN 201710691305A CN 107779207 B CN107779207 B CN 107779207B
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- Prior art keywords
- liquid crystal
- polymer
- crystal alignment
- formula
- linear
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 169
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 60
- 229920000642 polymer Polymers 0.000 claims abstract description 83
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 41
- 239000002904 solvent Substances 0.000 claims abstract description 40
- 229920001721 polyimide Polymers 0.000 claims abstract description 37
- 239000004642 Polyimide Substances 0.000 claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 claims abstract description 20
- 229920001400 block copolymer Polymers 0.000 claims abstract description 18
- -1 diamine compound Chemical class 0.000 claims description 77
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 62
- 150000004985 diamines Chemical class 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000002560 nitrile group Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 40
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 38
- 239000000758 substrate Substances 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 230000018044 dehydration Effects 0.000 description 10
- 238000006297 dehydration reaction Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 210000002858 crystal cell Anatomy 0.000 description 9
- 238000006068 polycondensation reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 6
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001840 cholesterol esters Chemical class 0.000 description 3
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 150000003949 imides Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- 229940075142 2,5-diaminotoluene Drugs 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
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- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 2
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 2
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 2
- JEAQJTYJUMGUCD-UHFFFAOYSA-N 3,4,5-triphenylphthalic acid Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C(C(O)=O)C(C(=O)O)=CC=1C1=CC=CC=C1 JEAQJTYJUMGUCD-UHFFFAOYSA-N 0.000 description 2
- OLQWMCSSZKNOLQ-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
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- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 description 2
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 description 2
- ASNOFHCTUSIHOM-UHFFFAOYSA-N 4-[10-(4-aminophenyl)anthracen-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(N)C=C1 ASNOFHCTUSIHOM-UHFFFAOYSA-N 0.000 description 2
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- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 description 1
- BZNLEPSVOGWFFQ-UHFFFAOYSA-N bis(4-aminophenyl) sulfate Chemical compound C1=CC(N)=CC=C1OS(=O)(=O)OC1=CC=C(N)C=C1 BZNLEPSVOGWFFQ-UHFFFAOYSA-N 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
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- DWQUPUUWCRSMLZ-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1(CCCCC1)C1=CC=CC=C1.C1(=CC=CC=C1)C1CCCCC1 DWQUPUUWCRSMLZ-UHFFFAOYSA-N 0.000 description 1
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- 230000007547 defect Effects 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
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- MYHGMWDKFGQECW-UHFFFAOYSA-N ethyl 2,4-diaminobenzoate Chemical compound CCOC(=O)C1=CC=C(N)C=C1N MYHGMWDKFGQECW-UHFFFAOYSA-N 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MVUXVDIFQSGECB-UHFFFAOYSA-N ethyl n-(3-triethoxysilylpropyl)carbamate Chemical compound CCOC(=O)NCCC[Si](OCC)(OCC)OCC MVUXVDIFQSGECB-UHFFFAOYSA-N 0.000 description 1
- MHBPZEDIFIPGSX-UHFFFAOYSA-N ethyl n-(3-trimethoxysilylpropyl)carbamate Chemical compound CCOC(=O)NCCC[Si](OC)(OC)OC MHBPZEDIFIPGSX-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
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- APWFJLJAQRZQIV-UHFFFAOYSA-N heptane-1,4-diamine Chemical compound CCCC(N)CCCN APWFJLJAQRZQIV-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- LIBWSLLLJZULCP-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)aniline Chemical compound CCO[Si](OCC)(OCC)CCCNC1=CC=CC=C1 LIBWSLLLJZULCP-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- ILRLVKWBBFWKTN-UHFFFAOYSA-N n-benzyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCC1=CC=CC=C1 ILRLVKWBBFWKTN-UHFFFAOYSA-N 0.000 description 1
- CLYWMXVFAMGARU-UHFFFAOYSA-N n-benzyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCC1=CC=CC=C1 CLYWMXVFAMGARU-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- VQXBKCWOCJSIRT-UHFFFAOYSA-N octadecane-1,12-diamine Chemical compound CCCCCCC(N)CCCCCCCCCCCN VQXBKCWOCJSIRT-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- IOXGEAHHEGTLMQ-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1.C1=CC=NN=C1 IOXGEAHHEGTLMQ-UHFFFAOYSA-N 0.000 description 1
- YMXFJTUQQVLJEN-UHFFFAOYSA-N pyrimidine Chemical compound C1=CN=CN=C1.C1=CN=CN=C1 YMXFJTUQQVLJEN-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- OAXARSVKYJPDPA-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC#C)CC1 OAXARSVKYJPDPA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1085—Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133723—Polyimide, polyamide-imide
Abstract
The invention relates to a liquid crystal aligning agent, which comprises a polymer (A) and a solvent (B), wherein the polymer (A) is selected from the group consisting of polyamic acid polymers, polyimide block copolymers and any combination of the above polymers. According to the liquid crystal alignment agent disclosed by the invention, a liquid crystal alignment film with good pretilt angle stability can be formed. In addition, the invention also provides a liquid crystal alignment film formed by the liquid crystal alignment agent, a manufacturing method of the liquid crystal alignment film and a liquid crystal display assembly comprising the alignment film.
Description
Technical Field
The present invention relates to a liquid crystal alignment agent and an application thereof, and more particularly, to a liquid crystal alignment agent capable of forming a liquid crystal alignment film with excellent pretilt angle stability, a liquid crystal alignment film formed from the liquid crystal alignment agent, and a liquid crystal display device having the liquid crystal alignment film.
Background
As the demand of consumers for the wide viewing angle characteristic of the lcd is increasing year by year, the demand of the electrical characteristic or the display characteristic of the lcd with a wide viewing angle is more severe than before.
The liquid crystal display device of the present invention is most widely used in a Vertical Alignment (Vertical Alignment) type. In the vertical alignment liquid crystal display device, the liquid crystal alignment film is used to align the liquid crystal molecules regularly and to make the liquid crystal molecules have a large tilt angle without providing an electric field. The liquid crystal alignment film is generally formed by coating a liquid crystal alignment agent containing a polymer material such as a polyamic acid polymer or a polyimide polymer on the surface of a substrate, and performing heat treatment and alignment treatment.
For example, Japanese patent application laid-open No. 2002-162630 discloses a polyamic acid polymer for a liquid crystal alignment film of a vertical alignment liquid crystal display device, which is obtained by polymerizing a diamine compound represented by formula (i) and a tetracarboxylic dianhydride compound.
Wherein T, U and V are each independently a benzene ring or a cyclohexane ring, and any H on the ring may be substituted with an alkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 3 carbon atoms and being substituted with fluorine, F, Cl or CN; m and n are each independently an integer of 0 to 2; h is an integer of 0 to 5; r is H, F, Cl, CN or a monovalent organic group; when m is 2 or n is 2, 2U's or 2V's may be the same or different.
At present, with the demand for high definition of liquid crystal display elements and reduction of contrast or residual charge of liquid crystal display elements, it is becoming important to improve voltage maintenance ratio or reduce residual charge when a dc voltage is applied and/or to early relax residual charge accumulated by the dc voltage when a liquid crystal alignment film is used.
In order to increase the voltage maintenance rate and to reduce the residual charge accumulated by the dc voltage as early as possible even after a long-term exposure at a high temperature, a liquid crystal aligning agent using a diamine compound containing a polyamic acid and/or a polyimide, which can be used as a raw material of the polyamic acid and the polyimide, is known (for example, see international publication No. WO2009093704 of the patent cooperation treaty).
However, in recent years, liquid crystal televisions with large screens and high definition have been widely used, and in liquid crystal display modules for these applications, it is necessary to have a characteristic of good pretilt angle stability under severe use environments as compared with display applications in which characters or still pictures are mainly displayed.
Therefore, it is an urgent need to solve the problem of the prior art to provide a liquid crystal alignment agent for a liquid crystal alignment film with good pretilt angle stability, so that the formed liquid crystal alignment film has better display quality when applied to a liquid crystal display device.
Disclosure of Invention
The liquid crystal alignment agent is obtained by using components of special polymers, and a liquid crystal alignment film and a liquid crystal display assembly formed by the liquid crystal alignment agent have the advantage of good pretilt angle stability.
Accordingly, the present invention relates to a liquid crystal aligning agent comprising:
a polymer (A); and
a solvent (B);
wherein the polymer (A) is selected from the group consisting of polyamic acid polymer, polyimide block copolymer, and any combination thereof; and is
The polymer (A) comprises units represented by the formula (Ia):
in the formula (Ia), Y is-COO-, -CONRd-or-Rj－NRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rjis a single bond or C1To C10Linear or branched alkylene of (a);
Rais a single bond or C1To C10Linear or branched alkylene of (a);
ht is a nitrogen-containing heterocycle;
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring;
a1 is an integer from 0 to 2; and
is a bonding site.
In the above-mentioned liquid crystal aligning agent, preferably, the polymer (A) comprises a unit represented by formula (Ia-1), formula (Ia-2) or formula (Ia-3):
y is-COO-, -CONRd-or-Rj－NRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rjis a single bond or C1To C10Linear or branched alkylene of (a);
Rais a single bond or C1To C10Linear or branched alkylene of (a);
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring;
a1 is an integer from 0 to 2; and
is a bonding site.
In the above liquid crystal aligning agent, the imidization ratio of the polymer (a) is preferably 35% to 85%.
The invention also provides a liquid crystal alignment film, which is prepared from the liquid crystal alignment agent.
The invention also provides a liquid crystal display component which comprises the liquid crystal alignment film.
The invention also provides a method for preparing the liquid crystal aligning agent, which comprises a mixed polymer (A) and a solvent (B);
wherein the polymer (A) is selected from the group consisting of polyamic acid polymer, polyimide block copolymer, and any combination thereof; and the polymer (A) is prepared by the reaction of a mixture comprising a tetracarboxylic dianhydride component (a) and a diamine component (b);
wherein the diamine component (b) comprises at least one diamine compound (b1) represented by the formula (Ib):
in the formula (Ib),
y is-COO-, -CONRd-or-Rj－NRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rjis a single bond or C1To C10Linear or branched alkylene of (a);
Rais a single bond or C1To C10Linear or branched alkylene of (a);
ht is a nitrogen-containing heterocycle;
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring; and
a1 is an integer from 0 to 2.
In the above-described method for producing a liquid crystal aligning agent, preferably, the diamine component (b) comprises a diamine compound (b1) represented by formula (Ib-1), formula (Ib-2) or formula (Ib-3):
wherein the content of the first and second substances,
y is-COO-, -CONRd-or-Rj－NRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rjis a single bond or C1To C10Linear or branched alkylene of (a);
Rais a single bond or C1To C10Linear or branched alkylene of (a);
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring; and
a1 is an integer from 0 to 2.
In the above-mentioned method for producing a liquid crystal aligning agent, the diamine compound (b1) represented by the formula (Ib) is preferably used in an amount of 3 to 40 moles based on 100 moles of the total amount of the diamine component (b) used.
In the above-mentioned method for producing a liquid crystal aligning agent, the solvent (B) is preferably used in an amount of 800 to 2500 parts by weight based on 100 parts by weight of the polymer (a).
In the above method for producing a liquid crystal aligning agent, the imidization ratio of the polymer (a) is preferably 35% to 85%.
The invention also provides a method for manufacturing the liquid crystal alignment film, which comprises forming the liquid crystal alignment film by the liquid crystal alignment agent, wherein the liquid crystal alignment agent is formed by the method for manufacturing the liquid crystal alignment agent.
The invention also provides a method for manufacturing a liquid crystal display device, the liquid crystal display device comprises a liquid crystal alignment film, the method for manufacturing the liquid crystal display device comprises the step of forming the liquid crystal alignment film by using the liquid crystal alignment agent, wherein the liquid crystal alignment agent is formed by the method for manufacturing the liquid crystal alignment agent.
Drawings
Fig. 1 is a side view of a liquid crystal display assembly according to an embodiment of the present invention.
Description of the symbols:
100 liquid crystal display assembly 110 first unit
112 first substrate 114 first conductive film
116 first liquid crystal alignment film 120 second cell
122 second substrate 124 second conductive film
126 second liquid crystal alignment film 130 liquid crystal cell
Detailed Description
The invention provides a liquid crystal alignment agent, which comprises:
a polymer (A); and
a solvent (B);
wherein the polymer (A) is selected from the group consisting of polyamic acid polymer, polyimide block copolymer, and any combination thereof; and is
The polymer (A) comprises units represented by the formula (Ia):
in the formula (Ia), Y is-COO-, -CONRd-or-Rj－NRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rjis a single bond or C1To C10Linear or branched alkylene of (a);
Rais a single bond or C1To C10Linear or branched alkylene of (a);
ht is a nitrogen-containing heterocycle;
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring;
a1 is an integer from 0 to 2; and
is a bonding site.
The polymer (A) according to the present invention is obtained by reacting a mixture comprising a tetracarboxylic dianhydride component (a) and a diamine component (b).
Specifically, the polymer (a) is selected from a polyamic acid polymer, a polyimide-based block copolymer, or any combination thereof. Wherein the polyimide block copolymer is selected from the group consisting of polyamic acid block copolymer, polyimide block copolymer, polyamic acid-polyimide block copolymer, and any combination thereof.
The polymer (A) comprises units represented by the formula (Ia):
in the formula (Ia), Y is-COO-, -CONRd-or-Rj－NRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rjis a single bond or C1To C10Linear or branched alkylene of (a);
Rais a single bond or C1To C10Linear or branched alkylene of (a);
ht is a nitrogen-containing heterocycle;
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring;
a1 is an integer from 0 to 2; and
is a bonding site.
Preferably, the polymer (A) comprises units of formula (Ia-1), formula (Ia-2) or formula (Ia-3):
y is-COO-, -CONRd-or-Rj－NRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rjis a single bond or C1To C10Linear or branched alkylene of (a);
Rais a single bond or C1To C10Linear or branched alkylene of (a);
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring;
a1 is an integer from 0 to 2; and
is a bonding site.
The tetracarboxylic dianhydride component (a) comprises at least one of an aliphatic tetracarboxylic dianhydride compound, an alicyclic tetracarboxylic dianhydride compound, an aromatic tetracarboxylic dianhydride compound, a tetracarboxylic dianhydride compound represented by the formulae (a-1) to (a-6), or a combination thereof.
Specific examples of the aliphatic tetracarboxylic dianhydride compound may include, but are not limited to, ethane tetracarboxylic dianhydride (ethyl tetracarboxylic dianhydride), butane tetracarboxylic dianhydride (butane tetracarboxylic dianhydride), or a combination of the above compounds.
Specific examples of the alicyclic tetracarboxylic dianhydride compound may include, but are not limited to, 1,2,3, 4-cyclobutanetetracarboxylic dianhydride, 1, 2-dimethyl-1, 2,3, 4-cyclobutanetetracarboxylic dianhydride, 1, 3-dichloro-1, 2,3, 4-cyclobutanetetracarboxylic dianhydride, 1,2,3, 4-tetramethyl-1, 2,3, 4-cyclobutanetetracarboxylic dianhydride, 1,2,3, 4-cyclopentanetetracarboxylic dianhydride, 1,2,4, 5-cyclohexanetetracarboxylic dianhydride, 3 ', 4, 4' -dicyclohexyltetracarboxylic dianhydride, cis-3, 7-dibutylcycloheptyl-1, 5-diene-1, 2,5, 6-tetracarboxylic dianhydride, 2,3, 5-tricarboxycyclopentylacetic dianhydride, bicyclo [2.2.2] -oct-7-ene-2, 3,5, 6-tetracarboxylic dianhydride, or a combination of the foregoing compounds.
Specific examples of the aromatic tetracarboxylic dianhydride compound may include, but are not limited to, 3, 4-dicarboxy-1, 2,3, 4-tetrahydronaphthalene-1-succinic dianhydride, pyromellitic dianhydride, 3 ', 4,4 ' -benzophenonetetracarboxylic dianhydride, 3 ', 4,4 ' -biphenylsulfone tetracarboxylic dianhydride, 1,4,5, 8-naphthalenetetracarboxylic dianhydride, 2,3,6, 7-naphthalenetetracarboxylic dianhydride, 3 ' -4,4 ' -diphenylethanetetracarboxylic dianhydride, 3 ', 4,4 ' -dimethyldiphenylsilanetetracarboxylic dianhydride, 3 ', 4,4 ' -tetraphenylsilanetetracarboxylic dianhydride, 1,2,3, 4-furantetracarboxylic dianhydride, 4,4 ' -bis (3, 4-dicarboxyphenoxy) diphenyl sulfide dianhydride, diphenyl sulfide dianhydride, 4,4 ' -bis (3, 4-dicarboxyphenoxy) diphenylsulfone dianhydride, 4,4 ' -bis (3, 4-dicarboxyphenoxy) diphenylpropane dianhydride (4,4 ' -bis (3, 4-dicarboxyphenoxy) diphenylpropane dianhydride), 3 ', 4,4 ' -perfluoroisopropylidene diphenyldioic dianhydride, 3 ', 4,4 ' -diphenyltetracarboxylic dianhydride, bis (benzenedioic acid) phenylphosphine oxide dianhydride, p-phenylene-bis (triphenylbenzenedioic acid) dianhydride, m-phenylene-bis (triphenylbenzenedioic acid) dianhydride, bis (triphenylbenzenedioic acid) -4,4 ' -diphenyl ether dianhydride, bis (triphenylbenzenedioic acid) -4,4 ' -diphenylmethane dianhydride, ethylene glycol-bis (anhydrotrimellitate), propylene glycol-bis (anhydrotrimellitate), 1, 4-butanediol-bis (anhydrotrimellitate), 1, 6-hexanediol-bis (anhydrotrimellitate), 1, 8-octanediol-bis (anhydrotrimellitate), 2-bis (4-hydroxyphenyl) propane-bis (anhydrotrimellitate), 2,3,4, 5-tetrahydrofurantetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5- (tetrahydro-2, 5-di-oxo-3-furanyl) -naphtho [1,2-c ] -furan-1, 3-dione { (1,3,3a,4,5,9b-hexahydro-5- (tetrahydro-2, 5-dioxy-3-furanyl) naphto [1,2-c ] furan-1,3-dione), 1,3,3a,4,5,9 b-hexahydro-5-methyl-5- (tetrahydro-2, 5-bisoxy-3-furanyl) -naphtho [1,2-c ] -furan-1, 3-dione, 1,3,3a,4,5,9 b-hexahydro-5-ethyl-5- (tetrahydro-2, 5-bisoxy-3-furanyl) -naphtho [1,2-c ] -furan-1, 3-dione, 1,3,3a,4,5,9 b-hexahydro-7-methyl-5- (tetrahydro-2, 5-bisoxy-3-furanyl) -naphtho [1,2-c ] -furan-1, 3-dione, 1,3,3a,4,5,9 b-hexahydro-7-ethyl-5- (tetrahydro-2, 5-bisoxyl-3-furyl) -naphtho [1,2-c ] -furan-1, 3-dione, 1,3,3a,4,5,9 b-hexahydro-8-methyl-5- (tetrahydro-2, 5-bisoxyl-3-furyl) -naphtho [1,2-c ] -furan-1, 3-dione, 1,3,3a,4,5,9 b-hexahydro-8-ethyl-5- (tetrahydro-2, 5-bisoxyl-3-furyl) -naphtho [1, an aromatic tetracarboxylic dianhydride compound such as 2-c ] -furan-1, 3-dione, 1,3,3a,4,5,9b-hexahydro-5, 8-dimethyl-5- (tetrahydro-2, 5-di-acetoxy-3-furyl) -naphtho [1,2-c ] -furan-1, 3-dione, 5- (2, 5-di-acetoxy-tetrahydrofuryl) -3-methyl-3-cyclohexene-1, 2-dicarboxylic dianhydride, or a combination of the above compounds.
The tetracarboxylic dianhydride compounds represented by the formulae (a-1) to (a-6) are shown below.
In the formula (a-5), A1Represents a divalent group containing an aromatic ring; r represents an integer of 1 to 2; a. the2And A3May be the same or different and may each independently represent-H or an alkyl group. Specific examples of the tetracarboxylic dianhydride compound represented by the formula (a-5) include at least one of the compounds represented by the formulae (a-5-1) to (a-5-3).
In the formula (a-6), A4Represents a divalent group containing an aromatic ring; a. the5And A6May be the same or different and each independently represents-H or an alkyl group. The tetracarboxylic dianhydride compound represented by the formula (a-6) is preferably a compound represented by the formula (a-6-1).
Preferably, the tetracarboxylic dianhydride component (a) includes, but is not limited to, 1,2,3, 4-cyclobutanetetracarboxylic dianhydride, 1,2,3, 4-cyclopentanetetracarboxylic dianhydride, 2,3, 5-tricarboxycyclopentylacetic dianhydride, 1,2,4, 5-cyclohexanetetracarboxylic dianhydride, 3, 4-dicarboxy-1, 2,3, 4-tetrahydronaphthalene-1-succinic dianhydride, pyromellitic dianhydride, 3 ', 4, 4' -benzophenone tetracarboxylic dianhydride, and 3,3 ', 4, 4' -biphenyl sulfone tetracarboxylic dianhydride. The tetracarboxylic dianhydride component (a) may be used alone or in combination of two or more.
The tetracarboxylic dianhydride component (a) is preferably used in an amount of 80 to 120 moles, more preferably 85 to 115 moles, based on 100 moles of the total diamine component (b).
The diamine component (b) according to the present invention comprises at least one diamine compound (b1) represented by the formula (Ib):
in the formula (Ib),
y is-COO-, -CONRd-or-Rj－NRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rjis a single bond or C1To C10Linear or branched alkylene of (a);
Raa single bond or is C1To C10Linear or branched alkylene of (a);
ht is a nitrogen-containing heterocycle;
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring; and
a1 is an integer from 0 to 2.
Preferably, the diamine component (b) comprises a diamine compound (b1) represented by the formula (Ib-1), the formula (Ib-2) or the formula (Ib-3):
wherein the content of the first and second substances,
y is-COO-),－CONRd-or-Rj－NRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rjis a single bond or C1To C10Linear or branched alkylene of (a);
Rais a single bond or C1To C10Linear or branched alkylene of (a);
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring; and
a1 is an integer from 0 to 2.
Specific examples of the diamine compound (b1) are
In the embodiment of the present invention, the diamine compound (b1) is used in an amount of 3 to 40 moles, preferably 5 to 35 moles, more preferably 5 to 30 moles, based on 100 moles of the total amount of the diamine component (b).
When the monomer for polymerization of the polymer (A) does not contain the diamine compound (b1), the prepared liquid crystal aligning agent has a defect of poor pretilt angle stability. When the amount of the diamine compound (b1) used is in the above range, a liquid crystal display device having excellent pretilt angle stability can be obtained.
Preferably, the diamine component (b) of the present invention may further comprise other diamine compounds (b 2).
The other diamine compound (b2) includes an aliphatic diamine compound, an alicyclic diamine compound, an aromatic diamine compound, a diamine compound having the formula (b2-1) to the formula (b2-26), or a combination thereof.
Specific examples of the aliphatic diamine compound include, but are not limited to, 1, 2-diaminoethane, 1, 3-diaminopropane, 1, 4-diaminobutane, 1, 5-diaminopentane, 1, 6-diaminohexane, 1, 7-diaminoheptane, 1, 8-diaminooctane, 1, 9-diaminononane, 1, 10-diaminodecane, 4' -diaminoheptane, 1, 3-diamino-2, 2-dimethylpropane, 1, 6-diamino-2, 5-dimethylhexane, 1, 7-diamino-2, 5-dimethylheptane, 1, 7-diamino-4, 4-dimethylheptane, 1, 7-diamino-3-methylheptane, 1, 3-diaminoheptane, 1, 7-diamino-3-methylheptane, 1, 7-diaminoheptane, 1, 4-dimethylheptane, 1, 7-diaminoheptane, 1, 4-diaminoheptane, 1, 7-diaminoheptane, 1, 3-methylheptane, 1, and 1, 9-diaminoheptane, 1, 9-diamino-5-methylnonane, 2, 11-diaminododecane, 1, 12-diaminooctadecane, 1, 2-bis (3-aminopropoxy) ethane, or combinations thereof.
Specific examples of the alicyclic diamine compound include, but are not limited to, 4 '-diaminodicyclohexylmethane, 4' -diamino-3, 3 '-dimethyldicyclohexylamine, 1, 3-diaminocyclohexane, 1, 4-diaminocyclohexane, isophoronediamine, tetrahydrodicyclopentadiene diamine, tricyclo [6.2.1.02,7] -undecene dimethyldiamine, 4' -methylenebis (cyclohexylamine), or a combination of the above compounds.
Specific examples of the aromatic diamine compound include, but are not limited to, 4 '-diaminodiphenylmethane, 4' -diaminodiphenylethane, 4 '-diaminodiphenylsulfone, 4' -diaminobenzanilide, 4 '-diaminodiphenylether, 3, 4' -diaminodiphenylether, 1, 5-diaminonaphthalene, 5-amino-1- (4 '-aminophenyl) -1,3, 3-trimethylindane, 6-amino-1- (4' -aminophenyl) -1,3, 3-trimethylindane, hexahydro-4, 7-methanoindanyldimethylenediamine, 3,3 '-diaminobenzophenone, 3, 4' -diaminobenzophenone, and the like, 4, 4' -diaminobenzophenone, 2-bis [4- (4-aminophenoxy) phenyl ] propane, 2-bis [4- (4-aminophenoxy) phenyl ] hexafluoropropane, 2-bis (4-aminophenyl) hexafluoropropane, 2-bis [4- (4-aminophenoxy) phenyl ] sulfone, 1, 4-bis (4-aminophenoxy) benzene, 1, 3-bis (3-aminophenoxy) benzene, 9-bis (4-aminophenyl) -10-hydroanthracene, 9,10-bis (4-aminophenyl) anthracene [9,10-bis (4-aminophenyl) anthrylene ], 2, 7-diaminofluorene, 2-bis [4- (4-aminophenoxy) phenyl ] hexafluoropropane, 2-bis (4-aminophenoxy) sulfone, 1, 4-aminophenoxy) benzene, 1, 3-bis (4-aminophenoxy) benzene, 9-bis (4-aminophenyl) -10-hydroanthrylene, 9,10-bis (4-aminophenyl) anthracene, 9, 9-bis (4-aminophenyl) fluorene, 4 ' -methylene-bis (2-chloroaniline), 4 ' - (p-phenyleneisopropyl) dianiline, 4 ' - (m-phenyleneisopropyl) dianiline, 2 ' -bis [4- (4-amino-2-trifluoromethylphenoxy) phenyl ] hexafluoropropane, 4 ' -bis [ (4-amino-2-trifluoromethyl) phenoxy ] -octafluorobiphenyl, 5- [4- (4-n-pentylalkylcyclohexyl) cyclohexyl ] phenyl-methylene-1, 3-diaminobenzene {5- [4- (4-n-pentylcyclohexylcyclohexyl ] phenylmethylene-1, 3-diaminobezene }, and mixtures thereof, 1,1-bis [4- (4-aminophenoxy) phenyl ] -4- (4-ethylphenyl) cyclohexane {1,1-bis [4- (4-aminophenyl) phenyl ] -4- (4-ethylphenyl) cyclohexane }, or a combination thereof.
The diamine compounds having the formulas (b2-1) to (b2-26) are shown below.
In the formula (B2-1), B1represents-O-),
B2Represents a group having a steroid (cholesterol) skeleton, a trifluoromethyl group, a fluoro group, an alkyl group having 2 to 30 carbon atoms, or a monovalent group derived from a nitrogen atom-containing cyclic structure such as pyridine, pyrimidine, triazine, piperidine, or piperazine.
Specific examples of the compound represented by the formula (b2-1) include, but are not limited to, ethyl 2, 4-diaminobenzoate (2,4-diaminophenyl ethyl formate), ethyl 3, 5-diaminobenzoate (3,5-diaminophenyl ethyl formate), propyl 2, 4-diaminobenzoate (2,4-diaminophenyl propyl formate), propyl 3,5-diaminophenyl formate (3,5-diaminophenyl propyl formate), 1-dodecyloxy-2, 4-diaminobenzene (1-dodecoxy-2, 4-diaminobenzophenone), 1-hexadecyloxy-2, 4-diaminobenzene (1-hexadecyloxy-2, 4-diaminobenzene), 1-octadecyloxy-2, 4-diaminobenzene (1-octadecoxy-2,4-diaminobenzene), At least one of the compounds represented by the formulae (b2-1-1) to (b2-1-6), or a combination of the above compounds.
The compounds represented by the formulae (b2-1-1) to (b2-1-6) are shown below.
In the formula (B2-2), B1And B in the formula (B2-1)1Same as B3And B4Each independently represents a divalent aliphatic ring, a divalent aromatic ring or a divalent heterocyclic group;
B5represents an alkyl group having 3 to 18 carbon atoms, an alkoxy group having 3 to 18 carbon atoms, a fluoroalkyl group having 1 to 5 carbon atoms, a fluoroalkoxy group having 1 to 5 carbon atoms, a cyano group or a halogen atom.
Specific examples of the compound represented by the formula (b2-2) include at least one of the compounds represented by the following formulae (b2-2-1) to (b 2-2-13):
in the formulae (b2-2-1) to (b2-2-13), s represents an integer of 3 to 12.
In the formula (B2-3), B6Each independently of the otherRepresents a hydrogen atom, an acyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a halogen atom, and B in each repeating unit6May be the same or different;
u represents an integer of 1 to 3.
Specific examples of the compound represented by the formula (b2-3) include when u is 1: p-diaminobenzene, m-diaminobenzene, o-diaminobenzene, 2, 5-diaminotoluene, or the like; when u is 2: 4,4 ' -diaminobiphenyl, 2 ' -dimethyl-4, 4 ' -diaminobiphenyl, 3 ' -dimethoxy-4, 4 ' -diaminobiphenyl, 2 ' -dichloro-4, 4 ' -diaminobiphenyl, 3 ' -dichloro-4, 4 ' -diaminobiphenyl, 2 ', 5,5 ' -tetrachloro-4, 4 ' -diaminobiphenyl, 2 ' -dichloro-4, 4 ' -diamino-5, 5 ' -dimethoxybiphenyl, or 4,4 ' -diamino-2, 2 ' -bis (trifluoromethyl) biphenyl; or when u is 3: 1, 4-bis (4' -aminophenyl) benzene, and the like.
Specific examples of the compound represented by the formula (b2-3) preferably include p-diaminobenzene, 2, 5-diaminotoluene, 4 '-diaminobiphenyl, 3' -dimethoxy-4, 4 '-diaminobiphenyl, 1, 4-bis (4' -aminophenyl) benzene or a combination of the above compounds.
In the formula (b2-4), v represents an integer of 2 to 12.
In the formula (b2-5), w represents an integer of 1 to 5.
The compound represented by the formula (b2-5) is preferably 4, 4' -diaminodiphenylsulfide.
In the formula (B2-6), B7And B9Each is independentRepresents a divalent organic group, and B7And B9May be the same or different;
B8represents a divalent group derived from a nitrogen atom-containing cyclic structure such as pyridine, pyrimidine, triazine, piperidine or piperazine.
In the formula (B2-7), B10、B11、B12And B13Each independently represents a hydrocarbon group having 1 to 12 carbon atoms, and B10、B11、B12And B13May be the same or different;
x1 each independently represents an integer of 1 to 3; and
x2 represents an integer of 1 to 20.
In the formula (B2-8), B14Represents an oxygen atom or a cyclohexylene group;
B15represents a methylene group;
B16represents a phenylene group or a cyclohexylene group; and
B17represents a hydrogen atom or a heptyl group.
Specific examples of the compound represented by the formula (b2-8) include a compound represented by the formula (b2-8-1), a compound represented by the formula (b2-8-2), or a combination of the above compounds:
the compounds represented by the formulae (b2-9) to (b2-25) are shown below.
In the formulae (B2-17) to (B2-25), B18Preferably represents an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms; b is19Preferably represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.
In the formula (B2-26), B20、B22Each independently represents a single bond, -O-, -COO-or-OCO-; b is21Is alkylene with 1 to 3 carbon atoms; b is23Is a single bond or an alkylene group having 1 to 3 carbon atoms. d and g each independently represent 0 or 1; e represents an integer of 0 to 2; f represents an integer of 1 to 20; wherein d and e are not 0 at the same time.
In the formula (B2-26), with "-B20-(B21-B22)gThe divalent group represented by- "is preferably an alkylene group having 1 to 3 carbon atoms, an-O-, -COO-or an-O-C group2H4-O- (wherein, represents a bond to a diaminophenyl group). With "-CfH2f+1The group represented by "is preferably linear. The two amino groups in the diaminophenyl group are preferably in the 2,4 or 3,5 positions relative to the other groups.
Specific examples of the compounds represented by the formula (b2-26) include compounds represented by the following formulae (b2-26-1) to (b 2-26-4):
the other diamine component (b2) may be used alone or in combination of plural kinds.
Specific examples of the other diamine component (b2) preferably include, but are not limited to, 1, 2-diaminoethane, 4 ' -diaminodicyclohexylmethane, 4 ' -diaminodiphenylmethane, 4 ' -diaminodiphenyl ether, 5- [4- (4-n-pentylcyclohexyl) cyclohexyl ] phenylmethylene-1,3-diaminobenzene, 1-bis [4- (4-aminophenoxy) phenyl ] -4- (4-ethylphenyl) cyclohexane, ethyl 2, 4-diaminobenzoate, 1-octadecyloxy-2, 4-diaminobenzene, a compound represented by the formula (b2-1-1), a compound represented by the formula (b2-1-2), a compound represented by the formula (b2-2-1), A compound represented by formula (b2-2-11), p-diaminobenzene, m-diaminobenzene, o-diaminobenzene, a compound represented by formula (b2-8-1), or a combination of the above compounds.
In the embodiment of the present invention, the other diamine compound (b2) is used in an amount of 60 to 97 moles, preferably 65 to 95 moles, more preferably 70 to 95 moles, based on 100 moles of the total amount of the diamine component (b) used.
The polymer (A) may include at least one of polyamic acid and polyimide. In addition, the polymer (A) may further include a polyimide-based block copolymer. The following further describes the preparation of the various polymeric compositions described above.
The polyamic acid is prepared by dissolving a mixture comprising a tetracarboxylic dianhydride component (a) and a diamine component (b) in a solvent and performing a polycondensation reaction at a temperature of 0 to 100 ℃. After the reaction for 1 to 24 hours, the reaction solution was distilled under reduced pressure with an evaporator to obtain polyamic acid. Alternatively, the reaction solution is poured into a large amount of a lean solvent to obtain a precipitate. Then, the precipitate was dried under reduced pressure to obtain a polyamic acid.
The tetracarboxylic dianhydride component (a) is used in an amount of 20 to 200 moles based on 100 moles of the diamine component (b); more preferably, the tetracarboxylic dianhydride component (a) is used in an amount of 30 to 120 moles.
The solvent used in the polycondensation reaction may be the same as or different from the solvent used in the liquid crystal aligning agent described below, and the solvent used in the polycondensation reaction is not particularly limited as long as it can dissolve the reactant and the product. The solvent preferably includes, but is not limited to, (1) aprotic polar solvents such as: aprotic polar solvents such as N-methyl-2-pyrrolidone (NMP), N-dimethylacetamide, N-dimethylformamide, dimethyl sulfoxide, γ -butyrolactone, tetramethylurea, hexamethylphosphoric triamide, and the like; or (2) phenolic solvents, such as: phenol solvents such as m-cresol, xylenol, phenol, and halogenated phenols. The solvent used in the polycondensation reaction is preferably used in an amount of 200 to 2000 parts by weight, and more preferably 300 to 1800 parts by weight, based on 100 parts by weight of the total amount of the mixture.
It is to be noted that, in the polycondensation reaction, the solvent may be used in combination with an appropriate amount of a poor solvent which does not cause precipitation of the polyamic acid. The lean solvent may be used singly or in combination of plural kinds, and it includes, but is not limited to, (1) alcohols such as: alcohols such as methanol, ethanol, isopropanol, cyclohexanol, ethylene glycol, propylene glycol, 1, 4-butanediol, and triethylene glycol; (2) ketones, for example: ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; (3) esters, for example: esters such as methyl acetate, ethyl acetate, butyl acetate, diethyl oxalate, diethyl malonate, or ethylene glycol ethyl ether acetate; (4) ethers, for example: ethers such as diethyl ether, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol n-propyl ether, ethylene glycol isopropyl ether, ethylene glycol n-butyl ether, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether; (5) halogenated hydrocarbons, for example: halogenated hydrocarbons such as dichloromethane, 1, 2-dichloroethane, 1, 4-dichlorobutane, trichloroethane, chlorobenzene, and o-dichlorobenzene; or (6) hydrocarbons, such as: hydrocarbons such as tetrahydrofuran, hexane, heptane, octane, benzene, toluene, xylene, or any combination of the above solvents. The lean solvent is used in an amount of preferably 0 to 60 parts by weight, and more preferably 0 to 50 parts by weight, based on 100 parts by weight of the diamine component (b).
The method for preparing the polyimide is to heat the polyamic acid prepared by the method for preparing the polyamic acid in the presence of a dehydrating agent and a catalyst. During heating, the amic acid functionality in the polyamic acid can be converted to imide functionality (i.e., imidization) via a dehydration dead-cycling reaction.
The solvent used in the dehydration dead cycle reaction may be the same as the solvent (B) in the liquid crystal aligning agent, and thus will not be described herein. The amount of the base polyamic acid used is 100 parts by weight, and the amount of the solvent used in the dehydration dead-cycle reaction is preferably 200 parts by weight to 2000 parts by weight, and more preferably 300 parts by weight to 1800 parts by weight.
In order to obtain a preferable imidization degree of the polyamic acid, the operating temperature of the dehydration dead-cycle reaction is preferably 40 to 200 ℃, more preferably 40 to 150 ℃. If the operation temperature of the dehydration dead-cycle reaction is lower than 40 ℃, the imidization reaction is not complete, and the imidization degree of the polyamic acid is reduced. However, if the operation temperature of the dehydration dead cycle reaction is higher than 200 ℃, the weight average molecular weight of the resulting polyimide is low.
The dehydrating agent used in the dehydration dead-cycle reaction may be selected from acid anhydride-based compounds, which are specifically exemplified by: acid anhydride compounds such as acetic anhydride, propionic anhydride and trifluoroacetic anhydride. The dehydrating solvent is used in an amount of 0.01 to 20 moles based on 1 mole of polyamic acid. The catalyst used in the dehydration dead-cycle reaction may be selected from (1) pyridines, for example: pyridine compounds such as pyridine, collidine and lutidine; (2) tertiary amine compounds, for example: and tertiary amine compounds such as triethylamine. The catalyst may be used in an amount of 0.5 to 10 moles based on 1 mole of the dehydrating agent.
In an embodiment of the present invention, the polymer composition (A) has an imidization ratio of 35% to 85%, preferably 40% to 85%, more preferably 40% to 80%. When the imidization ratio of the polymer composition (A) is in the above range, a liquid crystal display device having excellent pretilt angle stability can be obtained.
The polyimide block copolymer is selected from polyamic acid block copolymer, polyimide block copolymer, polyamic acid-polyimide block copolymer or any combination of the above polymers.
The polyimide-based block copolymer is preferably prepared by dissolving an initiator in a solvent and polycondensing the solution, wherein the initiator comprises at least one polyamic acid and/or at least one polyimide, and may further comprise a tetracarboxylic dianhydride component (a) and a diamine component (b).
The tetracarboxylic dianhydride component and the diamine component in the starting material may be the same as the tetracarboxylic dianhydride component (a) and the diamine component (B) used in the method for preparing polyamic acid, and the solvent used in the polycondensation reaction may be the same as the solvent (B) in the liquid crystal alignment agent described below, which is not described herein again.
The solvent used in the polycondensation reaction is preferably used in an amount of 200 to 2000 parts by weight, and more preferably 300 to 1800 parts by weight, based on 100 parts by weight of the starting material. The operation temperature of the polycondensation reaction is preferably 0 ℃ to 200 ℃, and more preferably 0 ℃ to 100 ℃.
The starting material preferably includes, but is not limited to, (1) two kinds of polyamic acids with different end groups and different structures; (2) two types of polyimide with different end groups and different structures; (3) polyamic acids and polyimides with different terminal groups and different structures; (4) the polyimide film comprises polyamic acid, a tetracarboxylic dianhydride component and a diamine component, wherein at least one of the tetracarboxylic dianhydride component and the diamine component is different from the structure of the tetracarboxylic dianhydride component and the diamine component used for forming the polyamic acid; (5) the polyimide comprises polyimide, a tetracarboxylic dianhydride component and a diamine component, wherein at least one of the tetracarboxylic dianhydride component and the diamine component is different from the structures of the tetracarboxylic dianhydride component and the diamine component used for forming the polyimide; (6) the polyimide film comprises polyamic acid, polyimide, a tetracarboxylic dianhydride component and a diamine component, wherein at least one of the tetracarboxylic dianhydride component and the diamine component is different from the structures of the tetracarboxylic dianhydride component and the diamine component used for forming the polyamic acid or the polyimide; (7) two structurally different polyamic acids, tetracarboxylic dianhydride components and diamine components; (8) two polyimide, tetracarboxylic dianhydride components and diamine components with different structures; (9) two polyamic acids and diamine components with end groups of anhydride groups and different structures; (10) two polyamic acid and tetracarboxylic dianhydride components with different structures and end groups of amino groups; (11) two polyimide and diamine components with end groups of anhydride groups and different structures; or (12) two polyimide and tetracarboxylic dianhydride components with different structures and end groups of amine groups.
Within the scope of not affecting the efficacy of the present invention, the polyamic acid, polyimide and polyimide-based block copolymer are preferably end-modified polymers with molecular weight adjusted first. By using the end-modified polymer, the coating property of the liquid crystal aligning agent can be improved. The mode of preparing the end-modified polymer can be prepared by adding a monofunctional compound while the polyamic acid is subjected to polycondensation reaction.
Specific examples of monofunctional compounds include, but are not limited to, (1) monobasic anhydrides such as: monobasic acid anhydrides such as maleic anhydride, phthalic anhydride, itaconic anhydride, n-decylsuccinic anhydride, n-dodecylsuccinic anhydride, n-tetradecylsuccinic anhydride and n-hexadecylsuccinic anhydride; (2) monoamine compounds, for example: monoamine compounds such as aniline, cyclohexylamine, n-butylamine, n-pentylamine, n-hexylamine, n-heptylamine, n-octylamine, n-nonylamine, n-decylamine, n-undecylamine, n-dodecylamine, n-tridecylamine, n-tetradecylamine, n-pentadecylamine, n-hexadecylamine, n-heptadecylamine, n-octadecylamine and n-eicosylamine; or (3) monoisocyanate compounds such as: monoisocyanate compounds such as phenyl isocyanate and naphthyl isocyanate.
The polymer (A) of the present invention has a polystyrene-reduced weight-average molecular weight of 2000 to 200000, preferably 3000 to 100000, more preferably 4000 to 50000, as measured by Gel Permeation Chromatography (GPC).
The solvent used in the liquid crystal aligning agent of the present invention is not particularly limited as long as it can dissolve the polymer (a) and other optional components and does not react with them, and it is preferably the same solvent as used in the synthesis of the polyamic acid described above, and a poor solvent used in the synthesis of the polyamic acid may be used in combination.
Specific examples of the solvent (B) include, but are not limited to, N-methyl-2-pyrrolidone, γ -butyrolactone, γ -butyrolactam, 4-hydroxy-4-methyl-2-pentanone, ethylene glycol monomethyl ether, butyl lactate, butyl acetate, methyl methoxypropionate, ethyl ethoxypropionate, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol N-propyl ether, ethylene glycol isopropyl ether, ethylene glycol N-butyl ether (ethylene glycol N-butyl ether), ethylene glycol dimethyl ether, ethylene glycol ethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate or N, N-dimethylformamide or N, N-dimethylacetamide (N, n-dimethyl acetamide), and the like. The solvent (B) may be used alone or in combination of two or more.
The solvent (B) is used in an amount of 800 to 2500 parts by weight, preferably 1000 to 2200 parts by weight, and more preferably 1000 to 2000 parts by weight, based on 100 parts by weight of the polymer (a).
The liquid crystal aligning agent may further optionally add an additive (C) within a range not affecting the efficacy of the present invention, wherein the additive (C) includes an epoxy compound, a silane compound having a functional group, or a combination thereof. The additive (C) serves to improve the adhesion of the liquid crystal alignment film to the substrate surface.
The epoxy compound includes, but is not limited to, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, glycerol diglycidyl ether, 2-dibromo neopentyl glycol diglycidyl ether, 1,3,5, 6-tetracyclooxypropyl-2, 4-hexanediol, N, N, N ', N ' -tetracyclooxypropyl-m-xylylenediamine, 1, 3-bis (N, N-diepoxylaminomethyl) cyclohexane, N, N, N ', N ' -tetracyclooxypropyl-4, 4 ' -diaminodiphenylmethane, 3- (N, N-diepoxypropyl) aminopropyltrimethoxysilane, or combinations of the foregoing.
The epoxy compound may be used alone or in combination of two or more.
The epoxy compound may be used in an amount of 0 to 40 parts by weight, and preferably 0.1 to 30 parts by weight, based on 100 parts by weight of the polymer (a).
Specific examples of the silane compound having a functional group include, but are not limited to, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 2-aminopropyltrimethoxysilane, 2-aminopropyltriethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, 3-ureidopropyltrimethoxysilane (3-uretropropyltrimethoxysilane), 3-ureidopropyltriethoxysilane, N-ethoxycarbonyl-3-aminopropyltrimethoxysilane, N-ethoxycarbonyl-3-aminopropyltriethoxysilane, N-triethoxysilylpropyltriethylenetriamine, N-aminopropyltriethoxysilane, N-aminopropyltrimethoxysilane, N-allyltrimethoxysilane, N-allylamine, N-allyltrimethoxysilane, N-allylamine, N-allylether-N-allylether-N-or N-N-N-N-N-N, N-trimethoxysilylpropyltriethylene triamine, 10-trimethoxysilyl-1, 4, 7-triazodecane, 10-triethoxysilyl-1, 4, 7-triazodecane, 9-trimethoxysilyl-3, 6-diazanonylacetate, 9-triethoxysilyl-3, 6-diazanonylacetate, N-benzyl-3-aminopropyltrimethoxysilane, N-benzyl-3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane, N-bis (oxyethylene) -3-aminopropyltriethoxysilane, or combinations of the foregoing.
The silane compound having a functional group may be used alone or in combination of two or more.
The silane compound having a functional group may be used in an amount of 0 to 10 parts by weight, and preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the polymer (a).
The additive (C) is preferably used in an amount of 0.5 to 50 parts by weight, and more preferably 1 to 45 parts by weight, based on 100 parts by weight of the polymer (a).
Method for preparing liquid crystal aligning agent
The method for producing the liquid crystal aligning agent is not particularly limited, and it can be produced by a general mixing method. For example, the tetracarboxylic dianhydride component (a) and the diamine component (b) are first mixed uniformly to react to form the polymer (a). Then, the polymer (A) is added into the solvent (B) at the temperature of 0 ℃ to 200 ℃, and optionally the additive (C) is added, and the mixture is continuously stirred by a stirring device until the polymer (A) is dissolved. Preferably, the solvent (B) is added to the polymeric composition at a temperature of from 20 ℃ to 60 ℃.
Preferably, the viscosity of the liquid crystal aligning agent of the present invention is generally 15cps to 35cps, preferably 17cps to 33cps, more preferably 20cps to 30cps at 25 ℃.
Method for manufacturing liquid crystal alignment film
The liquid crystal alignment film of the invention can be formed by the liquid crystal alignment agent.
Specifically, the liquid crystal alignment film may be prepared, for example, by: the liquid crystal alignment agent is applied to the surface of the substrate by a method such as a roll coating method, a spin coating method, a printing method, or an ink-jet method (ink-jet), to form a precoat layer. Next, the pre-coating layer is subjected to pre-bake treatment (pre-bake treatment), post-bake treatment (post-bake treatment), and alignment treatment (alignment treatment) to prepare a substrate on which a liquid crystal alignment film is formed.
The pre-baking treatment is intended to volatilize the organic solvent in the pre-coating layer. The operating temperature of the pre-baking treatment is preferably 30 ℃ to 120 ℃, and more preferably 40 ℃ to 110 ℃, and particularly preferably 50 ℃ to 100 ℃.
The alignment treatment is not particularly limited, and a cloth made of fibers such as nylon, rayon, or cotton may be wound around a drum and rubbed in a certain direction to perform alignment.
The post-bake treatment step is intended to further subject the polymer in the precoat to a dehydration dead cycle (imidization) reaction. The post-baking treatment is preferably carried out at an operating temperature of 150 ℃ to 300 ℃, more preferably 180 ℃ to 280 ℃, and most preferably 200 ℃ to 250 ℃.
Liquid crystal display module and method for manufacturing the same
The liquid crystal display component comprises a liquid crystal alignment film formed by the liquid crystal alignment agent. The manner of fabricating liquid crystal display devices is well known to those skilled in the art. Therefore, the following is only briefly stated.
Fig. 1 is a side view of a liquid crystal display assembly according to an embodiment of the present invention. The lcd assembly 100 includes a first unit 110, a second unit 120, and a liquid crystal unit 130, wherein the second unit 120 is disposed apart from the first unit 110, and the liquid crystal unit 130 is disposed between the first unit 110 and the second unit 120.
The first unit 110 includes a first substrate 112, a first conductive film 114 and a first liquid crystal alignment film 116, wherein the first conductive film 114 is formed on a surface of the first substrate 112. In addition, the first conductive film 114 is located between the first substrate 112 and the first liquid crystal alignment film 116, and the first liquid crystal alignment film 116 is located on one side of the liquid crystal cell 130.
The second unit 120 includes a second substrate 122, a second conductive film 124 and a second liquid crystal alignment film 126, wherein the second conductive film 124 is formed on the surface of the second substrate 122. In addition, the second conductive film 124 is located between the second substrate 122 and the second liquid crystal alignment film 126, and the second liquid crystal alignment film 126 is located on the other side of the liquid crystal cell 130. In other words, the liquid crystal cell 130 is located between the first liquid crystal alignment film 116 and the second liquid crystal alignment film 126.
The first substrate 112 and the second substrate 122 are selected from transparent materials, and the like, wherein the transparent materials include, but are not limited to, alkali-free glass, soda lime glass, hard glass (pyrex glass), quartz glass, polyethylene terephthalate, polybutylene terephthalate, polyethersulfone, polycarbonate, and the like used in liquid crystal display devices.
The material of the first conductive film 114 and the second conductive film 124 is selected from tin oxide (SnO)2) Indium oxide-tin oxide (In)2O3-SnO2) And the like.
The first liquid crystal alignment film 116 and the second liquid crystal alignment film 126 are the liquid crystal alignment films, and are used for forming a pre-tilt angle in the liquid crystal cell 130. In addition, when a voltage is applied to the first conductive film 114 and the second conductive film 124, an electric field may be generated between the first conductive film 114 and the second conductive film 124. The electric field drives the liquid crystal cell 130, thereby changing the arrangement of the liquid crystal molecules in the liquid crystal cell 130.
The liquid crystal used in the liquid crystal cell 130 may be used alone or in combination, and includes, but is not limited to, diaminobenzene-based liquid crystal, pyridazine (pyridazine) -based liquid crystal, schiff Base-based liquid crystal, azoxy-based liquid crystal, biphenyl (biphenyl) based liquid crystal, phenylcyclohexane (phenylcyclohexane) based liquid crystal, ester (ester) -based liquid crystal, terphenyl (terphenyl), diphenylcyclohexane (biphenylcyclohexane) based liquid crystal, pyrimidine (pyrimidine) based liquid crystal, dioxane-based liquid crystal, bicyclooctane (bicyclooctane) based liquid crystal, cubane (cubane) -based liquid crystal, etc., and cholesterol ester (cholesteryl chloride), cholesterol ester (cholesteryl nonoate), cholesterol carbonate (carboxide), etc., as the trade name of cholesterol ester CB, etc., or a methyl-15-decyl ether (methyl-2-15-methyl-2-or 15-methyl-decyl-2-methyl-2-or 15-methyl-decyl-2-methyl-2-ethyl-2-methyl-2-ethyl-cinnamyl-and the like, respectively, and the like, respectively A ferroelectric (ferrielectric) liquid crystal.
The invention is now described in detail by the following examples, which are not intended to limit the invention solely to the disclosure of these examples.
Preparation of Polymer (A):
synthesis example A-1
A four-necked flask having a volume of 500 ml was equipped with a nitrogen inlet, a stirrer, a condenser tube and a thermometer, and nitrogen gas was introduced thereinto. Then, 0.0005 mol of b1-1 shown in Table 1, 0.037 mol of p-diaminobenzene (abbreviated as b2-1), 0.0125 mol of b2-6 shown in Table 1, and 80 g of N-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone, abbreviated as NMP) were added to a four-necked flask and stirred at room temperature until dissolved. Then, 0.05 mole of 2,3, 5-tricarboxycyclopentylacetic dianhydride (abbreviated as a-1) and 20 g of NMP were added and reacted at room temperature for 2 hours. After the reaction was completed, the reaction solution was poured into 1500 ml of water to precipitate a polymer. Then, the obtained polymer was filtered, and washing with methanol and filtration were repeated three times, and the polymer (A-1-1) was obtained after drying at a temperature of 60 ℃ in a vacuum oven.
Synthesis examples A-1-2 to A-1-5
Synthesis examples A-1-2 to A-1-5 the polymers were prepared in the same procedure as in Synthesis example A-1-1, except that: the kind and amount of the tetracarboxylic dianhydride compound or the diamine compound used were changed as shown in table 1.
Synthesis example A-2-1
A four-necked flask having a volume of 500 ml was equipped with a nitrogen inlet, a stirrer, a condenser tube and a thermometer, and nitrogen gas was introduced thereinto. Then, 0.0015 moles of b1-1 shown in Table 1, 0.036 moles of p-diaminobenzene (abbreviated as b2-1), 0.0125 moles of b2-6 shown in Table 1, and 80 g of N-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone, abbreviated as NMP) were added to a four-necked flask and stirred at room temperature until dissolved. Next, 0.05 mole of 2,3, 5-tricarboxycyclopentylacetic dianhydride (referred to as a-1 for short) and 20 grams of NMP were added. After 6 hours of reaction at room temperature, 97 g of NMP, 2.55 g of acetic anhydride and 19.75 g of pyridine were added, and the mixture was heated to 60 ℃ and stirred for 2 hours to effect imidization. After the reaction was completed, the reaction solution was poured into 1500 ml of water to precipitate a polymer. Then, the obtained polymer was filtered, and washing with methanol and filtration were repeated three times, and the polymer (A-2-1) was obtained after drying at a temperature of 60 ℃ in a vacuum oven.
Synthesis examples A-2-2 to A-2-12 and comparative Synthesis examples A-4-1 to A-4-5
Synthesis examples A-2-2 to A-2-12 and comparative Synthesis examples A-4-1 to A-4-5 the polymers were prepared in the same procedure as in Synthesis example A-2-1, except that: the kinds and the amounts of the tetracarboxylic dianhydride component, the diamine component, the dehydrating agent or the catalyst used were changed as shown in table 1; and changing the types and the use amounts of the dehydrating agent and the catalyst for the dehydration dead cycle reaction.
Synthesis example A-3-1
A four-necked flask having a volume of 500 ml was equipped with a nitrogen inlet, a stirrer, a condenser tube and a thermometer, and nitrogen gas was introduced thereinto. Then, 0.0325 mol of p-diaminobenzene (abbreviated as b2-1) and 40 g of N-methyl-2-pyrrolidone (abbreviated as NMP) were added to a four-necked flask, and stirred at room temperature until dissolved. Next, 0.025 mol of pyromellitic dianhydride (referred to simply as a-3) and 10 g of NMP were added. After 6 hours of reaction at room temperature, 50 g of NMP, 1.3 g of acetic anhydride and 10 g of pyridine were added, and the mixture was heated to 60 ℃ and stirred for 2 hours to effect imidization. After the reaction was completed, the reaction solution was poured into 1500 ml of water to precipitate a polymer. Then, the obtained polymer was filtered, and washing with methanol and filtration were repeated three times, and the polymer (A-3-1-1) was obtained after drying at a temperature of 60 ℃ in a vacuum oven.
A four-necked flask having a volume of 500 ml was equipped with a nitrogen inlet, a stirrer, a condenser tube and a thermometer, and nitrogen gas was introduced thereinto. Then, the polymer (A-3-1-1) synthesized above, 0.0075 mol of b1-4 shown in Table 1, 0.01 mol of b2-6 shown in Table 1 and 100 g of NMP were added to a four-necked flask, and stirred at room temperature until dissolved. Then, 0.025 mole of 2,3, 5-tricarboxycyclopentylacetic dianhydride (abbreviated as a-1) and 10 g of NMP were added and reacted at room temperature for 2 hours. After the reaction was completed, the reaction solution was poured into 1500 ml of water to precipitate a polymer. Then, the obtained polymer was filtered, and washing with methanol and filtration were repeated three times, and the polymer (A-3-1) was obtained after drying at a temperature of 60 ℃ in a vacuum oven.
TABLE 2
In tables 1 and 2:
preparing a liquid crystal alignment agent, a liquid crystal alignment film and a liquid crystal display assembly:
example 1
100 parts by weight of the polymer (A-1-1) and 800 parts by weight of N-methyl-2-pyrrolidone (abbreviated as B-1) were weighed and mixed at room temperature with stirring to form the liquid crystal aligning agent of example 1.
The liquid crystal aligning agent was evaluated for each test item, and the results are shown in table 3.
Examples 2 to 18 and comparative examples 1 to 5
Examples 2 to 18 and comparative examples 1 to 5 were prepared in the same procedure as in example 1, except that: the polymer composition, the kind of solvent and the amount of the additive used were changed as shown in tables 3 and 4. The liquid crystal aligning agents were evaluated for each test item, and the results are shown in tables 3 and 4.
TABLE 3
TABLE 4
Tables 3 and 4:
detecting items:
imidization rate
The imidization ratio is a ratio of the number of imide rings calculated based on the total amount of the number of amic acid functional groups and the number of imide rings in the polyimide polymer, and is expressed as a percentage.
The imidization rate was measured at room temperature (e.g., 25 ℃ C.) using tetramethylsilane as a reference substance, after drying the polymer (A) of the above Synthesis examples A-1 to A-2-10 and comparative Synthesis examples A-3-1 to A-3-7 under reduced pressure, dissolving the polymer (A) in a suitable deuterated solvent (e.g., deuterated dimethyl sulfoxide)1From the results of H-NMR (hydrogen nuclear magnetic resonance), the imidization ratio (%) of the polymer (A) was calculated by the following formula:
in the formula, Δ 1 represents the peak area of NH group proton generated by chemical shift (chemical shift) around 10ppm, Δ 2 represents the peak area of other proton, and α represents the number ratio of 1 proton of NH group to other proton in polyamic acid precursor of the polymer in polymer composition (a).
Pretilt angle stability
The prepared liquid crystal aligning agent was applied to the transparent electrode surface of a glass substrate containing an ITO film (liquid crystal aligning film printing machine manufactured by Nippon ink-jet printing Co., Ltd.), heated on a hot plate at 80 ℃ for 1 minute (prebaking) to remove the solvent, and further heated on a hot plate at 150 ℃ for 10 minutes (after-baking), and the average film thickness was obtained
Coating film of (3). The coating film was put on a rubbing machine having a rayon cloth wound therearound and rubbed at a rotation speed of 400rpm, a traverse speed of 3 cm/sec and a fiber length of 0.1 mm. Then, the substrate was cleaned by ultrasonic cleaning in ultrapure water for 1 minute, and then dried in an oven at 100 ℃ for 10 minutes to obtain a substrate having a liquid crystal alignment film. Repeating the above steps to obtain 1 pair (2 pieces) of substrates with liquid crystal alignment films.
Then, the outer edge of the substrate with the liquid crystal alignment film is coated with an epoxy resin adhesive filled with alumina balls with the diameter of 5.5 μm, the surfaces of the liquid crystal alignment films are oppositely overlapped, and the adhesive is cured. Then, a nematic liquid crystal (MLC-6608, manufactured by merck) was filled from a liquid crystal injection port between 1 pair of substrates, and the liquid crystal injection port was sealed with an acrylic photo-curing adhesive, thereby obtaining a liquid crystal display module.
The liquid crystal cell prepared as described above was subjected to measurement of initial pretilt angle using a pretilt angle measuring instrument (Optipro, manufactured by Shintech), and the liquid crystal display element subjected to measurement of initial pretilt angle was irradiated at an irradiation dose of 10,000J/m2The evaluation was carried out by changing the pretilt angle before and after 20 hours under irradiation with a fluorescent lamp at 60 ℃ and an AC voltage of 20Vp-p, and the evaluation criteria were as follows:
very good: the variation of the pretilt angle is less than or equal to 1 degree;
o: the variation of the pretilt angle is more than 1 degree and less than or equal to 2 degrees;
x: the pretilt angle variation is > 2 deg.
The above embodiments are merely illustrative of the principles and effects of the present invention, and do not limit the present invention. Modifications and variations of the above-described embodiments may be made by those skilled in the art without departing from the spirit of the invention. The scope of the invention is to be determined by the following claims.
Claims (10)
1. A liquid crystal alignment agent comprising:
a polymer (A); and
a solvent (B);
wherein the polymer (A) is selected from the group consisting of polyamic acid polymer, polyimide block copolymer, and any combination thereof; and is
The polymer (A) comprises units represented by the formula (Ia-1), the formula (Ia-2) or the formula (Ia-3):
y is-COO-or-CONRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rais a single bond or C1To C10Linear or branched alkylene of (a);
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring;
a1 is an integer from 0 to 2; and
is a bonding site.
2. The liquid crystal aligning agent according to claim 1, wherein the imidization ratio of the polymer (A) is 35 to 85%.
3. A liquid crystal alignment film formed from the liquid crystal alignment agent according to claim 1 or 2.
4. A liquid crystal display device comprising the liquid crystal alignment film according to claim 3.
5. A method for preparing liquid crystal aligning agent, which comprises mixing polymer (A) and solvent (B);
wherein the polymer (A) is selected from the group consisting of polyamic acid polymer, polyimide block copolymer, and any combination thereof; and the polymer (A) is prepared by the reaction of a mixture comprising a tetracarboxylic dianhydride component (a) and a diamine component (b);
wherein the diamine component (b) comprises a diamine compound (b1) represented by the formula (Ib-1), the formula (Ib-2) or the formula (Ib-3):
wherein the content of the first and second substances,
y is-COO-or-CONRd－；
RdIs a hydrogen atom, or C1To C10Linear or branched alkyl of (a);
Rais a single bond or C1To C10Linear or branched alkylene of (a);
Rbis C1To C10A linear or branched alkoxy group, a nitrile group or a carbonyl group;
Rcis C1To C10Linear or branched alkyl of (a); or
RbAnd RcCan combine with each other to form a single ring; and
a1 is an integer from 0 to 2.
6. The method for producing a liquid crystal aligning agent according to claim 5, wherein the diamine compound (b1) represented by formula (Ib) is used in an amount of 3 to 40 moles based on 100 moles of the total amount of the diamine component (b) used.
7. The method for producing a liquid crystal aligning agent according to claim 5, wherein the solvent (B) is used in an amount of 800 to 2500 parts by weight based on 100 parts by weight of the polymer (A).
8. The method for producing a liquid crystal aligning agent according to claim 5, wherein the imidization ratio of the polymer (A) is 35 to 85%.
9. A method for producing a liquid crystal alignment film, comprising forming the liquid crystal alignment film from a liquid crystal aligning agent, wherein the liquid crystal aligning agent is formed by the method for producing a liquid crystal aligning agent according to any one of claims 5 to 8.
10. A method of manufacturing a liquid crystal display device comprising a liquid crystal alignment film, the method comprising forming the liquid crystal alignment film from a liquid crystal aligning agent, wherein the liquid crystal aligning agent is formed by the method of manufacturing a liquid crystal aligning agent according to any one of claims 5 to 8.
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| TW105127118A TWI687457B (en) | 2016-08-24 | 2016-08-24 | Liquid crystal alignment agent and use thereof |
| TW105127118 | 2016-08-24 |
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| JP2002162630A (en) * | 2000-11-29 | 2002-06-07 | Chisso Corp | Diamine compound and polymer material using the same, liquid crystal alignment layer using polymer material and liquid crystal display element equipped with alignment layer |
| KR20070035683A (en) * | 2005-09-28 | 2007-04-02 | 삼성전자주식회사 | Liquid crystal display and method for manufacturing the same |
| JP5663876B2 (en) * | 2008-01-25 | 2015-02-04 | 日産化学工業株式会社 | Liquid crystal aligning agent and liquid crystal display element using the same |
| KR101188777B1 (en) * | 2008-04-28 | 2012-10-10 | 제이에스알 가부시끼가이샤 | Liquid crystal aligning agent and method for forming liquid crystal alignment films, and polymers contained in the liquid crystal aligning agent |
| KR102073458B1 (en) * | 2009-07-21 | 2020-02-04 | 닛산 가가쿠 가부시키가이샤 | Diamine compound, polyamic acid, polyimide, and liquid crystal aligning agent |
| JP5751171B2 (en) * | 2009-12-14 | 2015-07-22 | 日産化学工業株式会社 | Liquid crystal alignment treatment agent and liquid crystal display element using the same |
| TWI520985B (en) * | 2012-07-18 | 2016-02-11 | 奇美實業股份有限公司 | Liquid crystal alignment agent, liquid crystal alignment film and liguid crystal display element |
| KR102125106B1 (en) * | 2012-08-29 | 2020-06-19 | 닛산 가가쿠 가부시키가이샤 | Liquid crystal alignment agent, liquid crystal alignment film, liquid crystal display element |
| TWI650345B (en) * | 2013-05-23 | 2019-02-11 | 日商日產化學工業股份有限公司 | Liquid crystal alignment treatment agent, liquid crystal alignment film, and liquid crystal display element |
| JP6361168B2 (en) * | 2013-06-17 | 2018-07-25 | Jsr株式会社 | Liquid crystal aligning agent, liquid crystal alignment film, liquid crystal display element, method for producing liquid crystal display element, polymer and compound |
| TWI527844B (en) * | 2014-06-06 | 2016-04-01 | 奇美實業股份有限公司 | Liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display device |
| CN105315463B (en) * | 2014-07-15 | 2019-11-26 | 捷恩智株式会社 | Polymer, aligning agent for liquid crystal, liquid crystal orientation film and liquid crystal display element |
| TWI534203B (en) * | 2014-07-24 | 2016-05-21 | 奇美實業股份有限公司 | Liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display device |
| JP2016139121A (en) * | 2015-01-22 | 2016-08-04 | Jsr株式会社 | Production method of liquid crystal alignment film and method for manufacturing liquid crystal element |
| CN107779206A (en) * | 2016-08-24 | 2018-03-09 | 奇美实业股份有限公司 | Liquid crystal aligning agent and manufacturing method thereof |
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| TW201807020A (en) | 2018-03-01 |
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